Quinazolines. VII. Synthesis of 1,3‐Diamino‐5,6‐dihydrobenzo[<i>f</i>]quinazolines

Rosowsky, A.; Chen, Katherine K. N.; Papathanasopoulos, Nickolas; Modest, Edward J.

doi:10.1002/jhet.5570090214

Cited by 17 publications

(3 citation statements)

References 31 publications

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“…NMR (DMSO-dg, 200 MHz): 1.27 (s, 9H, t-Bu), 7.76 (d, J = 9.0 Hz, 1H, Ar), 8.32 (d, J = 9.0 Hz, 1H, Ar), 8.65 (s, 1H, Ar), 10.21 (s, 1H, Ar), 11.40 (s, 1H, NH), 12.45 (br s, 1H, NH). (ii) JV-(9-Amino-l,2-dihydro-l-oxobenzo[/]quinazolin-3yl)pivalamide (17). The foregoing pivalamide 16 (0.18 g, 0.43 mmol) was dissolved in ethanol (200 mL) in a 500-mL Parr hydrogenation flask.…”

Section: -Amino-6-(methoxymethyl)benzo[/]quinazolin-l(2fl)one (4bb) (...mentioning

confidence: 99%

Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones

Pendergast¹,

Johnson²,

Dickerson³

et al. 1993

J. Med. Chem.

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The synthesis and thymidylate synthase (TS) inhibitory activity of a series of simple benzo[f]-quinazolin-1(2H)-ones are described. Fully aromatic 3-amino compounds with compact lipophilic substituents in the 9-position were found to have I50 values as low as 20 nM on the isolated enzyme, and represent the first examples of potent, folate-based TS inhibitors that completely lack any structural feature corresponding to the (p-aminobenzoyl)glutamate moiety of the cofactor. A number of the compounds also showed moderate growth inhibitory activity against a human colon adenocarcinoma cell line (SW480), with IC50 values as low as 2 microM.

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Section: -Amino-6-(methoxymethyl)benzo[/]quinazolin-l(2fl)one (4bb) (...mentioning

confidence: 99%

Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones

Pendergast¹,

Johnson²,

Dickerson³

et al. 1993

J. Med. Chem.

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“…6-(1-Adamantyl)-2-naphthol (10) was isolated by several radial chromatography techniques with petroleum ether/diethyl ether (95:5) as eluent from the crude product reaction mixture of anion 1 and 2 : 1 H NMR (CDCl 3 ) δ 1.80 (6H, m), 2.00 (6H, m), 2.13 (3H, m), 4.91 (1H, s), 7.02−7.11 (2H, m), 7.49−7.73 (4H, m); 13 C NMR (CDCl 3 ) δ 29.00, 36.14, 36.90, 43.18, 109.10, 117.48, 122.71, 124.81, 126.02, 128.99, 129.85, 132.79, 146.56, 152.92. MS (EI + ) 279 (20), 278(100), 221(65).…”

Section: Methodsmentioning

confidence: 99%

Fluorescent Quenching of the 2-Naphthoxide Anion by Aliphatic and Aromatic Halides. Mechanism and Consequences of Electron Transfer Reactions

Argüello

Peñéñory

2003

J. Org. Chem.

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The fluorescent excited state of the 2-naphthoxide ion (1) is quenched by aliphatic and aromatic halides according to an electron-transfer mechanism, with generation of the corresponding alkyl and aryl radicals by a concerted or consecutive C-X bond fragmentation reaction. Whereas bromo- and iodobenzene follow a concerted ET mechanism (C-X, BDE control), 1-bromonaphthalene exhibits a stepwise process (pi LUMO control). The photoinduced reaction of anion 1 with 1-iodoadamantane (2) in DMSO affords substitution products on C3, C6, and C8, 1-adamantanol, 1-adamantyl 2-naphthyl ether, and adamantane (3.2, 13.2, 12.2, 2.8, 2.5, and 14.1% yields, respectively). A complex mixture is also observed in the photochemical reaction of neopentyl iodide (3) with anion 1, which renders substitution on C1, C3, C6, C8, and 2-naphthyl neopentyl ether (8.1, 1.3, 19.1, 31.1, and 2.8% yields, respectively). The absence of reaction in the dark and the inhibition of the photoinduced reaction by the presence of the radical traps di-tert-butylnitroxide (DTBN) and 1,4-cyclohexadiene are evidence of a radical chain mechanism for these substitutions. On the other hand, only coupling at C1 is achieved by the photostimulated reaction of anion 1 with iodobenzene (5), to afford 41.9% of 1-phenyl-2-naphthol and 5.4% of disubstitution product. The regiochemistry of these reactions can be ascribed to steric hindrance and activation parameters.

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“…Recrystallization from aqueous EtOH gave 13 g (76%) of colorless plates: mp 110-111 °.Anal. (CigHzsNO) C, , N. l-Acetamido-4-n-hexyl-2-nitronaphthalene (13). A mixture of 11 (13 g, 0.047 mol) and urea (0.6 g) was dissolved in AC2O (10 ml) by warming at 40°.…”

Section: Methodsmentioning

confidence: 99%

Quinazolines. 12. 1,3-Diaminobenzo[f]quinazolines containing long-chain alkyl or chloro substituents on the central ring. Synthesis and biological evaluation as candidate antifolate and antimalarial agents

Rosowsky¹,

Huang²,

Papathanasopoulos³

et al. 1974

J. Med. Chem.

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Quinazolines. VII. Synthesis of 1,3‐Diamino‐5,6‐dihydrobenzo[f]quinazolines

Cited by 17 publications

References 31 publications

Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones

Benzoquinazoline inhibitors of thymidylate synthase: enzyme inhibitory activity and cytotoxicity of some 3-amino- and 3-methylbenzo[f]quinazolin-1(2H)-ones

Fluorescent Quenching of the 2-Naphthoxide Anion by Aliphatic and Aromatic Halides. Mechanism and Consequences of Electron Transfer Reactions

Quinazolines. 12. 1,3-Diaminobenzo[f]quinazolines containing long-chain alkyl or chloro substituents on the central ring. Synthesis and biological evaluation as candidate antifolate and antimalarial agents

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